Methanol → 2,4-Dichloro-6-methoxypyrimidine

HRID 1720770Notes

Reaction equation

HRID 1720770 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.CO.N1C(C)=CC(C)=CC=1C.C[CH2:22][O:23]CC>O1CCCC1>[CH3:22][O:23][C:6]1[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:9])[CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 79532,4,6-TrimethylpyridineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 38245092,4-Dichloro-6-methoxypyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4,6-trichloropyrimidine (55 g), methanol (50 ml) and collidine (50 g) is heated in dry tetrahydrofuran (400 ml) for 48 hr. Ether is added and the precipitate is collected. The precipitate is column chromatographed on silica gel to give 6-methoxy-2,4-dichloropyrimidine. This product is mixed with morpholine in THF and stirred at 20°-25° to give 6-methoxy-2-morpholino-4-chloropyrimidine. The 6-methoxy-2-morpholino-4-chloropyrimidine is heated with piperazine in pyridine at 60° for 24 hr to give the title compound.

Workup

  1. customthe precipitate is collected
  2. customchromatographed on silica gel

Sources & evidence

ORD record
ord-b9fd85a36da24bf4be643c57d8f4662c
Source dataset
uspto-grants-1996_04
Patent number
US05506354

Reaction notes

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